Nitromethane → HCID 55250532, compound

HRID 1963074Notes

Reaction equation

HRID 1963074 reaction equation
[F:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[N+:11]([CH3:14])([O-:13])=[O:12].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4](/[CH:5]=[CH:14]/[N+:11]([O-:13])=[O:12])[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27792353-Fluoro-2-methylbenzaldehyde

Product 1

HCID 55250532HCID 55250532, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A Knoevenagel condensation was carried out by stirring 3-fluoro-2-methyl-benzaldehyde (20.721 g, 150 mmol), nitromethane (48.75 ml, 900 mmol) and ammonium acetate (34.687 g, 450 mmol) in 300 ml of acetic acid at 115° C. for 3.5 h. The mixture was evaporated to dryness under reduced pressure and the residue was dissolved in 250 ml of EA. The solution was washed with water (250 ml), three times with a 1 N sodium hydroxide solution (125 ml) and with brine (125 ml), dried over magnesium sulfate, filtered and evaporated to dryness. 24.18 g of the title compound were obtained as a yellow solid.

Workup

  1. customA Knoevenagel condensation
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. dissolutionthe residue was dissolved in 250 ml of EA
  4. washThe solution was washed with water (250 ml), three times with a 1 N sodium hydroxide solution (125 ml) and with brine (125 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-f5896acb88f6439195860fde8793f111
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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